The deep-sea fungus Penicillium griseofulvum produces an extracellular polysaccharide, Ps1-1, when grown in potato dextrose-agar medium. Ps1-1 was isolated from the fermented broth using ethanol precipitation, anion-exchange and size-exclusion chromatography. Ps1-1 is a galactomannan with a molecular weight of about 20 kDa, and a molar ratio of mannose and glucose of 1.1:1.0. On the basis of one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) and mass spectroscopic analyses, Ps1-1 is composed of a long chain of galactofuranan and a mannose core. The galactofuranan chain consists of (1→5)-linked β-galactofuranose, with additional branches at C-6 consisting of (1→)-linked β-galactofuranose residues and phosphate esters. The mannan core is composed of (1→6)-linked α-mannopyranose substituted at C-2 by (1→)-linked α-mannopyranose residues, disaccharide and trisaccharide units of (1→2)-linked α-mannopyranose. The investigation demonstrated that Ps1-1 was a galactofuranose-containing galactomannan differing from previously described extracellular polysaccharides.

characterization, extracellular polysaccharide, preparation, deep-sea fungus, Penicillium griseofulvum

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
5	bDGalf	108.4	83.8	77.5	82.5	76.5	68.0
	bDGalf	108.2	82.5	77.5	82.5	76.5	60.5
5,6	bDGalf	109.0	82.5	77.5	82.5	70.4	60.5
5,6	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
5	bDGalf	5.21	7.16	4.12	4.17	3.89	3.69
	bDGalf	5.22	4.18	4.13	4.17	3.89	3.71-3.84
5,6	bDGalf	5.25	4.17	4.13	4.17	3.96	3.80
5,6	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
5	bDGalf	108.4/5.21	83.8/7.16	77.5/4.12	82.5/4.17	76.5/3.89	68.0/3.69
	bDGalf	108.2/5.22	82.5/4.18	77.5/4.13	82.5/4.17	76.5/3.89	60.5/3.71-3.84
5,6	bDGalf	109.0/5.25	82.5/4.17	77.5/4.13	82.5/4.17	70.4/3.96	60.5/3.80
5,6	P

There are 2 chemically distinct structures. Please, select:
-5)[P-6)]bDGalf(1-5)bDGalf(1- -5)[bDGalf(1-6)]bDGalf(1-5)bDGalf(1-

SVGMWSMILES3D molIonize

 

[*]O[C@H](COP(=O)(O)O)[C@@H]1O[C@@H](O[C@H](CO)[C@@H]2O[C@@H]([*])[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

404.261 g/mol (C₁₂H₂₁R₂O₁₃P, R = next and previous repeats, not counted in mol weight)

The deep-sea fungus Penicillium griseofulvum produces an extracellular polysaccharide, Ps1-1, when grown in potato dextrose-agar medium. Ps1-1 was isolated from the fermented broth using ethanol precipitation, anion-exchange and size-exclusion chromatography. Ps1-1 is a galactomannan with a molecular weight of about 20 kDa, and a molar ratio of mannose and glucose of 1.1:1.0. On the basis of one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) and mass spectroscopic analyses, Ps1-1 is composed of a long chain of galactofuranan and a mannose core. The galactofuranan chain consists of (1→5)-linked β-galactofuranose, with additional branches at C-6 consisting of (1→)-linked β-galactofuranose residues and phosphate esters. The mannan core is composed of (1→6)-linked α-mannopyranose substituted at C-2 by (1→)-linked α-mannopyranose residues, disaccharide and trisaccharide units of (1→2)-linked α-mannopyranose. The investigation demonstrated that Ps1-1 was a galactofuranose-containing galactomannan differing from previously described extracellular polysaccharides.

characterization, extracellular polysaccharide, preparation, deep-sea fungus, Penicillium griseofulvum

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]OC[C@H]1O[C@H]([*])[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O

648.564 g/mol (C₂₄H₄₀R₂O₂₀, R = next and previous repeats, not counted in mol weight)

Submerged culture of Auricularia auricula-judae has been documented, but there have been few studies on the structural characterization and medicinal properties of its exopolysaccharides. In present study, two exopolysaccharides, named CEPSN-1 and CEPSN-2, were isolated from submerged culture of A. auricula-judae, and their structural features as well as immunomodulatory activity were analyzed. The two exopolysaccharides both had a backbone chain composed of (1 → 4)-α-d-glucose residues in glucopyranose type. At the tested concentration range of 50-200 μg/mL, CEPSN-1 and CEPSN-2 not only showed non-toxicity to RAW 264.7 cells, but also could promote the release of NO and cytokines (IL-6, IL-10 and TNF-α) in the cells. The release of NO was significantly enhanced by the two exopolysaccharides at 100 μg/mL (p < 0.05). The IL-10 secretion was significantly increased by 1.80 and 1.61-fold, compared to the control after treatment with 50 μg/mL of CEPSN-1 and CEPSN-2, respectively (p < 0.05). These results demonstrated that, though their structural feature were different from that of polysaccharides from fruit body, exopolysaccharides of A. auricula-judae from submerged culture with the backbone of (1 → 4)-α-D-glucan could be explored as potential immunomodulatory agents for the application in complementary medicine or functional foods.

exopolysaccharides, immunomodulatory activity, Structural characterization, A. auricula-judae

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
	aDGlcp	100.1	71.6	73.5	77.1	71.2	60.7

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]O[C@@H]1[C@@H](CO)O[C@H]([*])[C@H](O)[C@H]1O

162.141 g/mol (C₆H₁₀R₂O₅, R = next and previous repeats, not counted in mol weight)